1H-Isoindole-1,3(2H)-dione, 2-[(1R)-2-hydroxy-1-phenylethyl]-

Base Information

• Chemical Name: 1H-Isoindole-1,3(2H)-dione, 2-[(1R)-2-hydroxy-1-phenylethyl]-
• CAS No.: 205380-30-9
• Molecular Formula: C16H13NO3
• Molecular Weight: 267.284
• DSSTox Substance ID: DTXSID20459531
• Nikkaji Number: J967.038F
• Wikidata: Q82283316
• Mol file: 205380-30-9.mol

Synonyms:205380-30-9;1H-Isoindole-1,3(2H)-dione, 2-[(1R)-2-hydroxy-1-phenylethyl]-;SCHEMBL16322141;DTXSID20459531;BSVAAYHIMWHTMM-AWEZNQCLSA-N;(R)-2-(2-hydroxy-1-phenylethyl)isoindoline-1,3-dione;2-[(1R)-1-Phenyl-2-hydroxyethyl]-2H-isoindole-1,3-dione

Chemical Property of 1H-Isoindole-1,3(2H)-dione, 2-[(1R)-2-hydroxy-1-phenylethyl]-

Chemical Property:

• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 267.08954328
• Heavy Atom Count: 20
• Complexity: 365

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(CO)N2C(=O)C3=CC=CC=C3C2=O
• Isomeric SMILES: C1=CC=C(C=C1)[C@H](CO)N2C(=O)C3=CC=CC=C3C2=O

Technology Process of 1H-Isoindole-1,3(2H)-dione, 2-[(1R)-2-hydroxy-1-phenylethyl]-

There total 4 articles about 1H-Isoindole-1,3(2H)-dione, 2-[(1R)-2-hydroxy-1-phenylethyl]- which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

phthalic anhydride (85-44-9) + D-2-phenylglycinol (56613-80-0) → (R)-2-(2-hydroxy-1-phenylethyl)-1H-isoindole-1,3(2H)-dione (205380-30-9)

Guidance literature:

at 140 - 150 ℃; for 4h;

DOI:10.1016/j.tet.2003.10.128

Reference yield:

N-((R)-2-Hydroxy-1-phenyl-ethyl)-phthalamic acid ethyl ester → (R)-2-(2-hydroxy-1-phenylethyl)-1H-isoindole-1,3(2H)-dione (205380-30-9)

Guidance literature:

With toluene-4-sulfonic acid; In tetrahydrofuran; for 12h; Yield given; Heating;

DOI:10.1055/s-1998-2038

Reference yield:

monoethyl phthalate (2306-33-4) → (R)-2-(2-hydroxy-1-phenylethyl)-1H-isoindole-1,3(2H)-dione (205380-30-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) PyBOP, (i-Pr)2NEt / 1.) THF, r.t., 40 min, 2.) THF, r.t.

2: p-TsOH / tetrahydrofuran / 12 h / Heating

With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran;

DOI:10.1055/s-1998-2038

upstream raw materials:

phthalic anhydride

D-2-phenylglycinol

monoethyl phthalate

Downstream raw materials:

3-Hydroxy-2-((R)-2-hydroxy-1-phenyl-ethyl)-3-methyl-2,3-dihydro-isoindol-1-one

(R)-2-(2-(benzyloxy)-1-phenylethyl)isoindoline-1,3-dione